Yeni bazı flavonoid türevlerinin sentezi, kimyasal yapılarının aydınlatılması ve monoamin oksidaz enzimleri üzerine etkilerinin araştırılması
Investigations on synthesis, chemical structure elucidation and effects on monoamine oxidase enzyme of some new flavonoid compounds
- Tez No: 267067
- Danışmanlar: PROF. DR. RAHMİYE ERTAN
- Tez Türü: Doktora
- Konular: Eczacılık ve Farmakoloji, Pharmacy and Pharmacology
- Anahtar Kelimeler: Docking, Hidrazon, MAO enzim inhibisyonu, 2-Pirazolin, Sentez ve yapı aydınlatma, Şalkon (prop-2-en-1-on) türevleri, Chalcone (prop-2-en-1-one) derivatives, Docking, Hydrazone, MAO enzyme inhibition, 2-Pyrazoline, Synthesis and structure elucidation
- Yıl: 2010
- Dil: Türkçe
- Üniversite: Ankara Üniversitesi
- Enstitü: Sağlık Bilimleri Enstitüsü
- Ana Bilim Dalı: Farmasötik Kimya Ana Bilim Dalı
- Bilim Dalı: Belirtilmemiş.
- Sayfa Sayısı: 322
Özet
Bu çalışmada, asetofenon (Ia-j) ve benzaldehit (IIa-d) türevlerinin metanol içinde KOH varlığında reaksiyonu ile şalkon türevleri (IIIa-u) elde edilmiş, elde edilen şalkonların etanol içinde hidrazit türevleriyle (IVa-f) ısıtılmasıyla hidrazon (Va-s) ve 2-pirazolin (VIa-u) yapısında bazı yeni moleküllerin sentezleri gerçekleştirilmiştir. Böylece şalkon (2), hidrazon (18) ve 2-pirazolin (20) türevleri olan toplam 40 orijinal kimyasal madde elde edilmiş ve bunların yapı tayinlerinde Elementel Analiz, IR, 1H-NMR ve Mass spektral yöntemlerinden yararlanılmıştır. Sentezlenen bileşiklerin, MAO enzimi üzerindeki inhibisyon yapıcı etkileri incelenmiş ve sonuçta VIa, VIc, VIf ve VIl bileşiklerinin referans bileşik moklobemide yakın düzeyde MAO-A enzimi üzerinde inhibisyon yapıcı etki gösterdikleri saptanmıştır. Sentezlenen orijinal bileşiklerin kimyasal okunuşları aşağıda bir arada verilmiştir;IIIc (E)-1-(3,5-dikloro-2-hidroksifenil)-3-m-tolilprop-2-en-1-onIIIo (E)-1-(4-bromofenil)-3-m-tolilprop-2-en-1-onVa (E)-N'-((E)-1-(2,4-dimetoksifenil)-3-p-tolilalliliden)tiyofen-2-karbohidrazidVb(E)-N'-((E)-1-(2,4-dimetoksifenil)-3-p-tolilalliliden)furan-2-karbohidrazidVc (E)-N'-((E)-1-(4-florofenil)-3-(4-metoksifenil)alliliden)tiyofen-2-karbohidrazidVd (E)-N'-((E)-1-(4-florofenil)-3-(4-metoksifenil)alliliden)-4-metil-1,2,3-tiyadiazol-5- karbohidrazidVe (E)-N'-((E)-1-(4-florofenil)-3-p-tolilalliliden)tiyofen-2-karbohidrazidVf (E)-N'-((E)-1-(4-florofenil)-3-m-tolilalliliden)tiyofen-2-karbohidrazidVg (E)-N'-((E)-1-(4-bromofenil)-3-p-tolilalliliden)tiyofen-2-karbohidrazidVh (E)-N'-((E)-1-(4-bromofenil)-3-p-tolilalliliden)-4-metil-1,2,3-tiyadiazol-5-karbohidrazidVi (E)-N'-((E)-1-(4-bromofenil)-3-(4-metoksifenil)alliliden)-4-metoksibenzohidrazidVj (E)-N'-((E)-1-(4-bromofenil)-3-m-tolilalliliden)-4-metil-1,2,3-tiyadiazol-5-karbohidrazidVk (E)-N'-((E)-1-(4-bromofenil)-3-(4-metoksifenil)alliliden)furan-2-karbohidrazidVl (E)-N'-((E)-1-(4-klorofenil)-3-p-tolilalliliden)tiyofen-2-karbohidrazidVm (E)-N'-((E)-1-(4-klorofenil)-3-p-tolilalliliden)-4-metil-1,2,3-tiyadiazole-5-karbohidrazidVn (E)-N'-((E)-1-(4-klorofenil)-3-m-tolilalliliden)-4-metil-1,2,3-tiyadiazole-5-karbohidrazidVo(E)-N'-((E)-1-(4-klorofenil)-3-(4-metoksifenil)alliliden)-4-metil-1,2,3-tiyadiazol-5-karbohidrazidVp (E)-N'-((E)-1-(4-klorofenil)-3-(4-metoksifenil)alliliden)-4-metoksibenzohidrazidVr (E)-N'-((E)-1-(4-hidroksifenil)-3-p-tolilalliliden)-4-metil-1,2,3-tiyadiazol-5- karbohidrazidVs (E)-N'-((E)-1-(4-metoksifenil)-3-p-tolilalliliden)-4-metil-1,2,3-tiyadiazol-5-karbohidrazidVIa(3-(5-kloro-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(piridin-4-il) metanonVIb (3-(5-kloro-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(furan-2- il)metanonVIc (3-(5-kloro-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(fenil) metanonVId (3-(5-kloro-2-hidroksifenill)-5-p-tolil-4,5-dihidropirazol-1-il)(4-metoksifenil) metanonVIe (3-(5-kloro-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(4-metil-1,2,3-tiyadiazol-5-il)metanonVIf (3-(3,5-dikloro-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(4-metoksifenil) metanonVIg (3-(3,5-dikloro-2-hidroksifenil)-5-m-tolil-4,5-dihidropirazol-1-il)(piridin-4-il) metanonVIh (3-(3,5-dikloro-2-hidroksifenil)-5-m-tolil-4,5-dihidropirazol-1-il)(furan-2-il) metanonVIi (3-(3,5-dikloro-2-hidroksifenil)-5-m-tolil-4,5-dihidropirazol-1-il)(fenil) metanonVIj (3-(3,5-dikloro-2-hidroksifenil)-5-m-tolil-4,5-dihidropirazol-1-il)(4-metoksifenil) metanonVIk (3-(3,5-dikloro-2-hidroksifenil)-5-m-tolil-4,5-dihidropirazol-1-il)(4-metil-1,2,3-tiyadiazol-5-il)metanonVIl (3-(5-bromo-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(piridin-4-il)metanonVIm (3-(5-bromo-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(furan-2-il) metanonVIn (3-(5-bromo-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(fenil)metanonVIo (3-(5-bromo-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(4-metoksifenil) metanonVIp (3-(5-Bromo-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(tiyofen-2-il) metanonVIr (3-(2-hidroksi-4-metoksifenil)-5-(2-metoksifenil)-4,5-dihidropirazol-1-il)(fenil) metanonVIs (3-(2-hidroksi-4-metoksifenil)-5-(4-metoksifenil)-4,5-dihidropirazol-1-il)(4-metoksifenil)metanonVIt (3-(5-bromo-2-hidroksifenil)-5-(4-metoksifenil)-4,5-dihidropirazol-1-il)(4-metoksifenil)metanonVIu (3-(5-kloro-2-hidroksifenil)-5-(4-metoksifenil)-4,5-dihidropirazol-1-il)(tiyofen-2-il) metanon
Özet (Çeviri)
In this study, chalcone derivatives (IIIa-u) were prepared with the reaction of some acetophenone (Ia-j) and benzaldehyde derivatives (IIa-d) in KOH/MeOH. The ensuing chalcone derivatives (IIIa-u) are then reacted with some hydrazide compounds to furnish hydrazone (Va-s) and 2-pyrazoline (VIa-u) derivatives. The structure of synthesized original chalcone (2), hydrazone (18) and 2-pyrazoline (20) derivatives was elucidated by IR, 1H NMR, Mass spectral data and elementary analysis findings. The synthesized compounds were tested for their MAO inhibitor activities and it is found that compounds VIa, VIc, VIf and VIl have similar activities as moclobemide. Chemical names of synthesized compounds are given below;IIIc (E)-1-(3,5-Dichloro-2-hydroxyphenyl)-3-m-tolylprop-2-en-1-oneIIIo (E)-1-(4-Bromophenyl)-3-m-tolylprop-2-en-1-onVa (E)-N'-((E)-1-(2,4-Dimethoxyphenyl)-3-p-tolylallylidene)thiophene-2-carbohydrazideVb (E)-N'-((E)-1-(2,4-Dimethoxyphenyl)-3-p-tolylallylidene)furan-2-carbohydrazideVc (E)-N'-((E)-1-(4-Fluorophenyl)-3-(4-methoxyphenyl)allylidene)thiophene-2-carbohydrazideVd (E)-N'-((E)-1-(4-Fluorophenyl)-3-(4-methoxyphenyl)allylidene)-4-methyl-1,2,3-thiadiazole-5-carbohydrazideVe (E)-N'-((E)-1-(4-Fluorophenyl)-3-p-tolylallylidene)thiophene-2-carbohydrazideVf (E)-N'-((E)-1-(4-Fluorophenyl)-3-m-tolylallylidene)thiophene-2-carbohydrazideVg (E)-N'-((E)-1-(4-Bromophenyl)-3-p-tolylallylidene)thiophene-2-carbohydrazideVh (E)-N'-((E)-1-(4-Bromophenyl)-3-p- tolylallylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazideVi (E)-N'-((E)-1-(4-Bromophenyl)-3-(4-methoxyphenyl)allylidene)-4-methoxy benzohydrazideVj (E)-N'-((E)-1-(4-Bromophenyl)-3-m-tolylallylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazideVk (E)-N'-((E)-1-(4-Bromophenyl)-3-(4-methoxyphenyl)allylidene)furan-2-carbohydrazideVl (E)-N'-((E)-1-(4-Chlorophenyl)-3-p-tolylallylidene)thiophene-2-carbohydrazideVm (E)-N'-((E)-1-(4-Chlorophenyl)-3-p-tolylallylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazideVn (E)-N'-((E)-1-(4-Chlorophenyl)-3-m-tolylallylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazideVo (E)-N'-((E)-1-(4-Chlorophenyl)-3-(4-metoxyphenyl)allylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazideVp (E)-N'-((E)-1-(4-Chlorophenyl)-3-(4-metoxypheny)allylidene)-4-metoxybenzohidrazideVr (E)-N'-((E)-1-(4-Hydroxyphenyl)-3-p-tolylallylidene)-4-methyl-1,2,3-thiadiazole-5- carbohidrazideVs (E)-N'-((E)-1-(4-Metoxyphenyl)-3-p-tolylallylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazideVIa(3-(5-Chloro-2-hidroxyphenyl)-5-p-tolyl-4,5-dihydropyrazole-1-yl)(pyridine-4-yl) methanoneVIb (3-(5-Chloro-2-hidroxyphenyl)-5-p-tolyl-4,5-dihydropyrazole-1-yl)(furan-2- yl)methanoneVIc (3-(5-Chloro-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazole-1-yl)(phenyl) methanoneVId (3-(5-Chloro-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazole-1-yl)(4-metoxyphenyl) methanoneVIe (3-(5-Chloro-2-hydroxyphenyl)-5-p-tolyl-4,5-dihidropyrazole-1-yl)(4-methyl-1,2,3-thiadiazole-5-yl)methanoneVIf (3-(3,5-Dichloro-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazole-1-yl)(4-metoxyphenyl) methanoneVIg (3-(3,5-Dichloro-2-hydroxyphenyl)-5-m-tolyl-4,5-dihidropyrazole-1-il)(pyridine-4-il) metanoneVIh (3-(3,5-Dichloro-2-hydroxyphenyl)-5-m-tolyl-4,5-dihidropyrazole-1-yl)(furan-2-yl) methanoneVIi (3-(3,5-Dichloro-2-hydroxyphenyl)-5-m-tolyl-4,5-dihydropyrazole-1-yl)(phenyl) methanoneVIj (3-(3,5-Dichloro-2-hydroxyphenyl)-5-m-tolyl-4,5-dihydropyrazole-1-yl)(4-metoxyphenyl) methanoneVIk (3-(3,5-Dichloro-2-hydroxyphenyl)-5-m-tolyl-4,5-dihydropyrazole-1-yl)(4-methyl-1,2,3-thiadiazole-5-yl)methanoneVIl (3-(5-Bromo-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazol-1-yl)(pyridine-4-yl)methanoneVIm (3-(5-Bromo-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazol-1-yl)(furan-2-yl) methanoneVIn (3-(5-Bromo-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazol-1-yl)(phenyl)methanoneVIo (3-(5-Bromo-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazol-1-yl)(4-metoxyphenyl) methanoneVIp (3-(5-Bromo-2-hydroxypheny)-5-p-tolyl-4,5-dihydropyrazol-1-yl)(thiophene-2-yl) methanoneVIr (3-(2-Hydroxy-4-metoxyphenyl)-5-(2-metoxyphenyl)-4,5-dihydropyrazol-1-yl)(phenyl) methanoneVIs (3-(2-Hydroxy-4-metoxyphenyl)-5-(4-metoxyphenyl)-4,5-dihydropyrazol-1-yl)(4-metoxyphenyl)methanoneVIt (3-(5-Bromo-2-hydroxyphenyl)-5-(4-metoxyphenyl)-4,5-dihydropyrazol-1-yl)(4-metoxyphenyl)methanoneVIu (3-(5-Chloro-2-hydroxyphenyl)-5-(4-metoxyphenyl)-4,5-dihydropyrazol-1-yl)(thiophen-2-yl) methanone
Benzer Tezler
- Yeni bazı biyolojik etkili flavonoid sentezleri üzerinde araştırmalar (B halkasında moleküler modifikasyon)
Başlık çevirisi yok
MERAL TUNÇBİLEK
Doktora
Türkçe
1994
Eczacılık ve FarmakolojiAnkara ÜniversitesiFarmasötik Kimya Ana Bilim Dalı
PROF.DR. RAHMİYE ERTAN
- Antidiyabetik etkili yeni bazı kimyasal bileşikler üzerinde araştırmalar
Studies on some chemical compounds with antidiabetic activity
DÜNDAR BOZDAĞ
Doktora
Türkçe
1998
Eczacılık ve FarmakolojiAnkara ÜniversitesiFarmasötik Kimya Ana Bilim Dalı
PROF. DR. RAHMİYE ERTAN
- Yeni bazı antimikrobiyal etkili kromon türevlerinin sentezi, yapı aydınlatması ve biyolojik aktivite tayini
Synthesis, structure elucidation and biological activity determination of some new antimicrobial effective chromone derivatives
FİRDEVS KÜBRA ARSLAN
Yüksek Lisans
Türkçe
2024
KimyaAnkara ÜniversitesiFarmasötik Kimya Ana Bilim Dalı
DOÇ. DR. MELTEM ÜNLÜSOY
- Flavonil azol içeren yeni bazı antifungal bileşikler üzerine sentez çalışmaları
Investigations on some new antifungal flavonyl azole compounds
BEGÜM EVRANOS
Yüksek Lisans
Türkçe
2004
Eczacılık ve FarmakolojiAnkara ÜniversitesiFarmasötik Kimya Ana Bilim Dalı
PROF.DR. RAHMİYE ERTAN
- Combinatorial libraries of stilbene fused chalcone and flavanone derivatives: Synthesis and anti-proliferative properties
Stilben kaynaştırılmış çalkon ve flavanon türevlerinin tümleşik kütüphaneleri: Sentez ve anti-proliferatif özellikler
İSMAİL AKÇOK
Yüksek Lisans
İngilizce
2009
Kimyaİzmir Yüksek Teknoloji EnstitüsüKimya Ana Bilim Dalı
YRD. DOÇ. DR. ALİ ÇAĞIR